Imidazole → 5-(tert-Butyldimethylsilyloxy)-1H-indole

HRID 1359938Notes

Reaction equation

HRID 1359938 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.N1C=CN=C1.[Si:16](Cl)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]>C(Cl)Cl>[Si:16]([O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 160545-HydroxyindoleHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 222508175-(tert-Butyldimethylsilyloxy)-1H-indole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 5-hydroxyindole in DCM (0.3 M) was added imidazole (2.0 eq). The mixture was cooled to 0° C. and treated with tert-butyldimethylsilyl chloride (1.0 eq). The resulting mixture was stirred at room temperature for 12 h, diluted with DCM, washed sequentially with H2O, 1N HCl (aq) and finally with brine. The combined organic fractions were dried over Na2SO4. The crude was purified by column chromatography on silica gel (Petroleum ether:Diethyl ether 90/10) to afford the title compound as a white solid.

Workup

  1. washwashed sequentially with H2O, 1N HCl (aq) and finally with brine
  2. dry with materialThe combined organic fractions were dried over Na2SO4
  3. customThe crude was purified by column chromatography on silica gel (Petroleum ether:Diethyl ether 90/10)

Sources & evidence

ORD record
ord-cb5791dce5be4a33bad9482526a0f903
Source dataset
uspto-grants-2011_02
Patent number
US07879815B2

Reaction notes

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